Objective: This article describes how using media depictions of psychotherapy may help in teaching psychiatric residents. Methods: Using the HBO series "In Treatment" as a model, the authors suggest how boundary transgressions and technical errors may inform residents about optimal psychotherapeutic approaches. Results: The psychotherapy vignettes depicted in "In Treatment" show how errors in judgment may grow out of therapists' good intentions. These errors can be understood and used constructively for teaching. Conclusion: With the growing interest in depicting psychotherapy on popular TV series, the use of these sessions avoids confidentiality problems and may be a useful adjunct for teaching psychotherapy.